EP 1092432 A1 20010418 - Anti-ischemic compounds
Title (en)
Anti-ischemic compounds
Title (de)
Anti-ischämische Verbindungen
Title (fr)
Composes anti-ischemiques
Publication
Application
Priority
EP 99870212 A 19991015
Abstract (en)
Acyclic, mono- or bicyclic malonic acid amide, ester or thioester derivatives (I) are new. Malonic acid amide, ester or thioester derivatives of formula (I) and their salts and prodrugs are new. n = 1 or 2; R1 = CH2, NH or a ligand (preferably a C atom) forming a 5-6C aromatic or non-aromatic ring (optionally containing a heteroatom, specifically N, O or S); R3, R4 = NR5R6 or ZR6; Z = O or S; R5 = H or 1-6C alkyl (preferably Me or Et); R6 = hydrophobic group, preferably tert. butyl, allyl or 5-7C aromatic or non-aromatic ring, optionally containing heteroatom(s) and optionally C-substituted by R7, keto, OH, ester residue, halo, CF3 or a heterocyclic group of formula (a); W = CH or N; Y = O or S; R7, R8 = 1-6C alkyl (preferably Me or Et); and provided that if R3 + R1 = ring as defined above or if R3 = NR5R6 or ZR6, then R4 = optionally unsaturated 1-10C alkyl (optionally containing heteroatom(s)). An Independent claim is also included for the preparation of (I).
Abstract (fr)
La présente invention concerne un composé de formule (I), un sel éventuel ou une prodrogue de celui-ci correspondant à la formule I : <IMAGE> ainsi que son application pour la prévention et/ou le traitement de l'ischémie partielle ou totale ou de pathologies associées à l'ischémie ou associées à des déficiences mitochondriales.
IPC 1-7
A61K 31/165; A61K 31/225; A61K 31/365; C07D 307/93; C07C 69/38; C07C 233/07; C07C 235/74; A61P 9/10
IPC 8 full level
A61K 31/165 (2006.01); A61K 31/225 (2006.01); A61K 31/365 (2006.01); A61P 9/10 (2006.01); C07C 69/013 (2006.01); C07C 69/38 (2006.01); C07C 233/07 (2006.01); C07C 235/74 (2006.01); C07D 307/93 (2006.01)
CPC (source: EP US)
A61P 9/10 (2017.12 - EP); C07C 69/013 (2013.01 - EP US); C07C 235/74 (2013.01 - EP US); C07D 307/93 (2013.01 - EP US)
Citation (search report)
- [X] WO 8705898 A2 19871008 - RHONE POULENC BV [NL]
- [X] EP 0099091 A1 19840125 - TAKEDA CHEMICAL INDUSTRIES LTD [JP]
- [X] FR 2539412 A1 19840720 - OZAKI SHOICHIRO [JP]
- [X] WO 9716184 A1 19970509 - WARNER LAMBERT CO [US], et al
- [A] WO 9937294 A2 19990729 - MITOKOR [US], et al
- [X] UKRAINETS, IGOR V. ET AL: "Ethyl esters of malonanilic acids. Synthesis and pyrolysis", TETRAHEDRON (1994), 50(34), 10331-8, XP002130231
- [X] VENUTI, MICHAEL C. ET AL: "Inhibitors of cyclic AMP phosphodiesterase. 4. Synthesis and evaluation of potential prodrugs of lixazinone (N-cyclohexyl-N-methyl-4-[(1,2,3,5- tetrahydro-2-oxoimidazo[2,1-b]quinazolin-7-yl)oxy]butyramide, RS-82856)", J. MED. CHEM. (1988), 31(11), 2145-52, XP000872883
- [X] H. OUMAR-MAHAMAT ET AL.: "Mn(III)-mediated Radical Lactonisation of Allylic Esters of Acetoacetic and Malonic acids", TETRAHEDRON LETTERS, vol. 30, no. 3, 1989, pages 331 - 332, XP002130465
- [X] HOLLOWOOD J ET AL: "LOCAL ANESTHETICS WITH ENHANCED AFFINITY FOR PROTEINS", JOURNAL OF MEDICINAL CHEMISTRY,US,AMERICAN CHEMICAL SOCIETY. WASHINGTON, vol. 10, no. 5, 1 September 1967 (1967-09-01), pages 863 - 867, XP002036645, ISSN: 0022-2623
- [X] MCLAUGHLIN B A ET AL: "Toxicity of dopamine to striatal neurons in vitro and potentiation of cell death by a mitochondrial inhibitor.", JOURNAL OF NEUROCHEMISTRY, (1998 JUN) 70 (6) 2406-15., XP000872545
Designated contracting state (EPC)
AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE
DOCDB simple family (publication)
EP 1092432 A1 20010418; AU 783713 B2 20051201; AU 7919200 A 20010430; CA 2387164 A1 20010426; EP 1225883 A1 20020731; US 6780887 B1 20040824; WO 0128549 A1 20010426
DOCDB simple family (application)
EP 99870212 A 19991015; AU 7919200 A 20001011; CA 2387164 A 20001011; EP 0010085 W 20001011; EP 00969499 A 20001011; US 11066202 A 20020730